# Lenny Playbooks

> Curated skill combinations for specific roles - founder, PM, manager, growth leader, and more. Each playbook combines essential Lenny skills.

- Skill: `leolin990405/lenny-playbooks` (Agent Skill)
- Install (CLI): `npx skillmds@latest add leolin990405/lenny-playbooks`
- Raw SKILL.md: https://api.skillmd.com/api/skills/leolin990405/lenny-playbooks/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Marketing & Growth
- Author: LeoLin990405 (https://skillmd.com/u/leolin990405)
- Updated: 2026-09-17
- Page: https://skillmd.com/skills/leolin990405/lenny-playbooks

---


# Lenny Playbooks - Role-Based Skill Combinations

Curated collections of Lenny skills for specific roles and career stages. Each playbook combines essential skills from the base Lenny skill categories.

## Available Playbooks

### 1. Startup Founder Playbook
**For:** First-time founders, early-stage startup leaders
**Stage:** Pre-seed to Series A

**Core Skills (from lenny-* categories):**
- `lenny-startup`: Fundraising Strategy, Startup Pivoting, Designing Team Rituals
- `lenny-hiring`: Writing Job Descriptions, Conducting Interviews, Building Team Culture
- `lenny-strategy`: Defining Product Vision, Writing North Star Metrics, Prioritizing Roadmap
- `lenny-growth`: Measuring Product-Market Fit, Designing Growth Loops
- `lenny-sales`: Founder Sales
- `lenny-execution`: Shipping Products, Managing Timelines

**Key Focus Areas:**
1. Find product-market fit before scaling
2. Build the founding team
3. Raise capital strategically
4. Ship fast and iterate

---

### 2. First-Time Manager Playbook
**For:** Individual contributors transitioning to management
**Stage:** First management role

**Core Skills:**
- `lenny-hiring`: Running Effective 1:1s, Having Difficult Conversations, Delegating Work
- `lenny-communication`: Written Communication, Stakeholder Alignment
- `lenny-decision`: Running Effective Meetings, Post-mortems & Retrospectives
- `lenny-career`: Managing Imposter Syndrome
- `lenny-advanced`: Coaching Product Managers, Energy Management

**Key Focus Areas:**
1. Shift from doing to enabling
2. Build trust through 1:1s
3. Learn to delegate effectively
4. Develop your management style

---

### 3. Product Manager Playbook
**For:** PMs at any level
**Stage:** All career stages

**Core Skills:**
- `lenny-strategy`: Writing PRDs, Problem Definition, Scoping & Cutting, Setting OKRs & Goals
- `lenny-research`: Conducting User Interviews, Usability Testing, Analyzing User Feedback
- `lenny-execution`: Shipping Products, Cross-functional Collaboration
- `lenny-communication`: Giving Presentations, Stakeholder Alignment
- `lenny-advanced`: Developing Product Taste, Systems Thinking

**Key Focus Areas:**
1. Define problems worth solving
2. Understand users deeply
3. Ship with quality and speed
4. Influence without authority

---

### 4. Growth Leader Playbook
**For:** Growth PMs, Growth marketers, Growth leads
**Stage:** Post-PMF companies

**Core Skills:**
- `lenny-growth`: Measuring Product-Market Fit, Designing Growth Loops, Retention & Engagement, Pricing Strategy
- `lenny-research`: Designing Surveys, Analyzing User Feedback
- `lenny-marketing`: Launch Marketing, Content Marketing, Community Building
- `lenny-advanced`: User Onboarding, Behavioral Product Design
- `lenny-technology`: AI Product Strategy

**Key Focus Areas:**
1. Build sustainable growth loops
2. Optimize activation and retention
3. Experiment systematically
4. Scale what works

---

### 5. Engineering Manager Playbook
**For:** Tech leads becoming managers, Engineering managers
**Stage:** First EM role or scaling teams

**Core Skills:**
- `lenny-hiring`: Conducting Interviews, Evaluating Candidates, Onboarding New Hires
- `lenny-design`: Engineering Culture, Platform & Infrastructure, Design Systems
- `lenny-technology`: Technical Roadmaps, Managing Tech Debt
- `lenny-decision`: Running Decision Processes, Evaluating Trade-offs
- `lenny-communication`: Running Offsites

**Key Focus Areas:**
1. Build high-performing engineering teams
2. Balance technical debt and features
3. Create strong engineering culture
4. Develop technical leaders

---

### 6. Sales Leader Playbook
**For:** Sales managers, VP Sales, CROs
**Stage:** Building or scaling sales teams

**Core Skills:**
- `lenny-sales`: Founder Sales, Building Sales Team, Enterprise Sales, Partnership & BD
- `lenny-startup`: Sales Compensation Design, Sales Qualification
- `lenny-hiring`: Writing Job Descriptions, Conducting Interviews
- `lenny-communication`: Giving Presentations, Stakeholder Alignment
- `lenny-strategy`: Competitive Analysis

**Key Focus Areas:**
1. Build repeatable sales processes
2. Hire and develop sales talent
3. Design effective compensation
4. Scale enterprise sales

---

### 7. AI Builder Playbook
**For:** AI/ML PMs, AI engineers, AI startup founders
**Stage:** Building AI-first products

**Core Skills:**
- `lenny-technology`: AI Product Strategy, Building with LLMs, AI Evaluation (Evals), Evaluating New Technology
- `lenny-strategy`: Writing PRDs, Problem Definition
- `lenny-research`: Conducting User Interviews, Usability Testing
- `lenny-advanced`: Vibe Coding, Dogfooding
- `lenny-growth`: Measuring Product-Market Fit

**Key Focus Areas:**
1. Design for AI's strengths and weaknesses
2. Build robust evaluation frameworks
3. Ship AI products users love
4. Stay ahead of rapid capability changes

---

### 8. Executive Communication Playbook
**For:** Directors, VPs, C-suite executives
**Stage:** Senior leadership roles

**Core Skills:**
- `lenny-communication`: Giving Presentations, Written Communication, Stakeholder Alignment, Running Offsites, Media Relations
- `lenny-decision`: Running Decision Processes, Planning Under Uncertainty
- `lenny-hiring`: Managing Up, Building a Promotion Case
- `lenny-marketing`: Brand Storytelling, Positioning & Messaging

**Key Focus Areas:**
1. Communicate with clarity and impact
2. Align stakeholders at scale
3. Build executive presence
4. Navigate organizational politics

---

### 9. Career Growth Playbook
**For:** Anyone looking to advance their career
**Stage:** All career stages

**Core Skills:**
- `lenny-career`: Startup Ideation, Managing Imposter Syndrome, Personal Productivity, Organizational Transformation
- `lenny-hiring`: Building a Promotion Case, Negotiating Offers, Finding Mentors & Sponsors, Career Transitions
- `lenny-advanced`: Energy Management
- `lenny-communication`: Written Communication, Giving Presentations

**Key Focus Areas:**
1. Build skills before you need them
2. Create visibility for your work
3. Find mentors and sponsors
4. Navigate career transitions

---

## How to Use Playbooks

### Quick Start
Ask me to help with a specific playbook:
- "Use the Startup Founder playbook to help me with fundraising"
- "Apply the PM playbook to write a PRD for [feature]"
- "Use the First-Time Manager playbook for my first 1:1"

### Combining Skills
Playbooks automatically combine relevant skills. For example:
- "I'm a founder preparing for Series A" → Combines startup, hiring, strategy, and communication skills
- "I'm a new PM at a growth-stage company" → Combines PM, growth, and execution skills

### Custom Playbooks
You can request custom combinations:
- "Create a playbook for a technical PM at an AI startup"
- "What skills do I need as a PM transitioning to founder?"

## Skill Dependencies

```
lenny-playbooks
├── lenny-hiring (13 skills)
├── lenny-strategy (10 skills)
├── lenny-growth (4 skills)
├── lenny-research (4 skills)
├── lenny-marketing (5 skills)
├── lenny-sales (4 skills)
├── lenny-communication (5 skills)
├── lenny-decision (5 skills)
├── lenny-execution (3 skills)
├── lenny-technology (6 skills)
├── lenny-design (5 skills)
├── lenny-advanced (12 skills)
├── lenny-career (5 skills)
└── lenny-startup (5 skills)
```

## Source
[Lenny's Podcast Playbooks](https://refoundai.com/lenny-skills/playbooks/) | [Lenny's Podcast](https://www.lennyspodcast.com/)

